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Beachfront vacation rentals in Sunset Key

Find and book unique beachfront homes on Airbnb

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Popular amenities for Sunset Key beachfront rentals

Pet-friendly beachfront home rentals

Top guest favorite
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars2 days ago
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.
Superhost
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars3 months ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
Guest favorite
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars2 months ago
Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars3 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Guest favorite
Home in Marathon
4.9 out of 5 average rating, 31 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

Stanley JamesRating, 5 stars1 month ago
Amazing location, great house with lots of space, cute artistic touches and we really appreciated the sharp knives! The screened in lanai was fantastic! Highly recommend! We’d come back in a heartbeat!
Guest favorite
Home in Cudjoe Key
4.93 out of 5 average rating, 54 reviews

Private Ocean Oasis by Key West, Florida

EricaRating, 5 stars2 weeks ago
Just what our family needed. As a new Florida resident it’s safe to say the Keys rank up there as one of my favorite places to visit. Rhonda’s home felt like our home. We enjoyed the pool and bikes. A local restaurant The Bent Prop bar and grill was a treasured find. My husband and I met the owner who is from the same area as us in Maryland. If you’ve ever wondered what Maryland Cream of Crab soup taste like… that’s the place to get it from! Can’t wait to book us again for next year!
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars4 weeks ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 141 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

MichaelRating, 5 stars3 weeks ago
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.

Beachfront home rentals with a pool

Guest favorite
Home in Cudjoe Key
4.9 out of 5 average rating, 52 reviews

Keys Island Villa - Venture Out Home 354

ClaudiaRating, 5 stars1 month ago
Fantastic stay w great views. House made us feel right at home. place was in gated community. it felt safe and well maintained. Fun to walk around in the evenings.
Superhost
Condo in Key West
4.6 out of 5 average rating, 83 reviews

Beautifully Renovated Summer of 2020 Come and enjo

CristinaRating, 5 stars2 months ago
The experience was so memorable! Just the R&R our family needed!
Superhost
Home in Marathon
5 out of 5 average rating, 8 reviews

Sandbox

MikeRating, 5 stars3 months ago
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.
Superhost
Condo in Key West
5 out of 5 average rating, 6 reviews

Galleon Resort - Walk to Duval & Mallory Square!

PatriciaRating, 5 stars5 months ago
Incredible view! Place was clean and what we expected. Gorgeous unit right on the water. Watching the boats go by was so relaxing. Tiki bar right below us was convenient if we wanted a drink while relaxing. Had a small problem with the dryer and they came to fix it within the hour, so I was more than satisfied with upkeep. Walk to restaurants and hot spots was easy. Great Irish pub a block away (Celtic Conch). Unit is convenient for any type of boating excursion you would like to book as the boardwalk/marina is right there. Chris, our host, was very responsive to any questions we had and very helpful in booking arrangements. We did not have recommendation questions for him, as we’ve been to key west a number of times and have friends who live there, but I’m sure based on the dealings we had with him, he’d be happy to help. One note, this is a timeshare community. I was worried we’d be hounded. We were not.
Guest favorite
Home in Marathon
5 out of 5 average rating, 6 reviews

Chiquita Waterfront Home

ShanaeRating, 5 stars1 week ago
My family and I really enjoyed this home the pictures do not do it justice it’s beautiful. The owners are very responsive and we were even able to check in a day early ! The canal was awesome , a boat is a must and so much fun. We saw manatees and iguanas. The private pool was fun all together a great experience.
Guest favorite
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Top guest favorite
Home in Cudjoe Key
4.96 out of 5 average rating, 25 reviews

Tiki Time in Cudjoe Key 136

LorriRating, 5 stars3 weeks ago
Pretty view and well stocked
Guest favorite
Apartment in Key West
5 out of 5 average rating, 5 reviews

Henry's Penthouse On The Ocean

WilliamRating, 5 stars1 month ago
The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.

Private beachfront home rentals

Top guest favorite
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Top guest favorite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars2 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Guest favorite
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Ocean Escape 97

LisaRating, 5 stars1 month ago
Omg what can’t I say about the house. Beautiful! Very friendly neighborhood. Extremely clean and beautifully maintained. The host were available and responded so quickly. We loved it and will be back! Thank you so much for sharing paradise with us!
Guest favorite
Home in Summerland Key
4.75 out of 5 average rating, 8 reviews

Sailfish Dream on Cudjoe Key-28 day minimum

DougRating, 5 stars2 months ago
Had a very comfortable and enjoyable stay. Accommodations were excellent. Weather was excellent! Warm balmy breezes most days kept humidity down. Lots to do, explored the keys from Islamorada down to Key West, caught the sunset. Spotted deer on Big Pine Key. A very fine month long vacation. Thank you Jeanene.
Superhost
Condo in Key West
4.92 out of 5 average rating, 24 reviews

Key West's Crown Jewel

JulieRating, 5 stars5 months ago
We had the best time at the Crown Jewel. Property was exactly as described—perfect condition. Bed was super comfortable. Patio view was unbeatable. The property management company was extremely communicative and helpful. Would absolutely recommend!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

NuciaRating, 5 stars1 month ago
We had a wonderful family vacation getaway at Katie and Cody’s place. The house was very clean, and the location is great as well with accessibility to food, Publix, and great beaches. Our favorite aspect of the house was the small pool. Our teenagers played in it endlessly, and when they were gone we enjoyed relaxing on the pool floats. Communication with Katie was top notch. She always responded quickly and had great follow through with any issues we had. they definitely go above and beyond to provide resources of fun activities and resteraunts in the area. We would definitely stay here again!
Superhost
Home in Key West
4.6 out of 5 average rating, 55 reviews

Brisa Del Mar by AvantStay | Ocean Front Community

RebekahRating, 5 stars2 months ago
Very cute condo. The location was great, we had an ocean view which was wonderful. It was easy to find. It was perfect for a couples getaway. Beds were comfortable but the pillows were not. AC can’t go below 75.
Superhost
Houseboat in Stock Island
5 out of 5 average rating, 4 reviews

Great Ocean Views! No regrets

Victor And TinaRating, 5 stars1 month ago
First time staying on a houseboat and it surely was a great experience! Beautiful views and comfy cozy space! Hosts were very friendly and welcoming and available with any questions we had. Thanks for a lovely experience!

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Sunset Key
  7. Beachfront rentals